(-)-Mandelic acid → (2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide(R)-(-)-mandelate

HRID 1887760Notes

Reaction equation

HRID 1887760 reaction equation
[NH2:1][C:2]([CH3:38])([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:8])=[O:4].[C:39]([OH:49])(=[O:48])[C@@H:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:41]>C(OCC)(=O)C>[C:39]([OH:49])(=[O:48])[C@@H:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:41].[NH2:1][C:2]([CH3:37])([CH3:38])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 11914(-)-Mandelic acidHCID 59620332(2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

Product 1

HCID 89723348(2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide(R)-(-)-mandelate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

(2R)-2-(2-Amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide (542 mg) was dissolved in ethyl acetate (6.5 mL), and (R)-(−)-mandelic acid (141 mg) was added thereto. The mixture was stirred at 70° C. for 10 minutes, and then left to stand to cool to room temperature. The formed precipitates were recovered through filtration, washed with ethyl acetate, and dried under reduced pressure, whereby the title compound (589 mg) was yielded.

Workup

  1. waitleft
  2. temperatureto cool to room temperature
  3. customThe formed precipitates
  4. filtrationwere recovered through filtration
  5. washwashed with ethyl acetate
  6. dry with materialdried under reduced pressure, whereby the title compound (589 mg)
  7. customwas yielded

Sources & evidence

ORD record
ord-58fa7b80c0f14491ae87c54c98c8bfbc
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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